You should be fine on most quiet side streets in CS. At the top of the main street before the Burway starts to veer right, there's a little strip of grass with a cut through behind it. I've seen Boners park there, but be early for it.
Plenty of places to grab meals (Ragleth, Bridges, the pub at Picklescott that I don't remember the name of, Jemimas for brekky). But sensible to carry backup snacks.
You won't be far between pubs. The longest section is probably the Stiperstones/Eastridge/Port Way part, but you could top up water at the pub in Picklescott if you're bone dry.
Midge is usually minimal. But anything can happen.